9: One Fine Day 

New York

Photo: 20th Century Fox

Aww, this is yet another of my teenage years pick. Michelle Pfeiffer and George Clooney co-star as respective single parents with very different parenting styles. They are forced into a kind of “co-parenting” scenario over the course of one day when their kids miss a field trip. A young Mae Whitman (The DUFF) co-stars.

You can buy One Fine Day on DVD.

Content Note: This film rates PG for some mild profanity and sensuality.

10: Pillow Talk

New York

Photo: Universal-International

In one of their many pair ups, Doris Day and Rock Hudson co-star as opposites who fall in love over a shared phone line in this classic madcap romantic-comedy from 1959.

Rent or buy Pillow Talk on Amazon Video.

Content Note: This film is “not rated.” It may contain some minor innuendo.


11: Sabrina

It’s been an age since I watched this film. Its got a kind of fairy tale quality and tells the story of a young girl who grows up as the daughter of an employee of a wealthy family. When she returns as an adult, she finds herself in the middle of a love triangle involving the two sons of her father’s former employer. Which version do you like best? The 1950s (Humphrey Bogart, Audrey Hepburn) or 1990s (Harrison Ford, Julia Ormond) adaptation?

Find Sabrina (1995) on Amazon Prime (at this publication).

Content Note: This 1995 film is PG for some adult situations.

12: Serendipity

About a year (or so) ago, I finally watched this film (for the first time). It’s not a favorite romantic-comedy, but it’s all about the swoons and I appreciate its quirky nature. Plus, it doesn’t hurt that many of the romance scenes happen against a snowy backdrop in New York City.

Rent Serendipity on Amazon Video.

Content Note: This film rates PG13 for adult situations and some profanity.

13: Set it Up

Set It Up

Photo: Netflix

Of course, I have to mention this charmer! A recent Netflix original, Set It Up follows two overworked assistants who decide to set up their respective bosses in the hope they’ll get more free time.

Stream Set It Up on Netflix

Content Note: This film is rated TV14 for some sexual situations and profanity.

14: You’ve Got Mail

New York

Photo: Warner Bros.

Though this one is universally loved by many, it’s not my favorite. Still, I find it a cute little pick-me-up now and again, and who doesn’t love the whole “you-brought-me-daisies” scene? Meg Ryan and Tom Hanks re-team (from Sleepless in Seattle) for this romantic comedy about two people falling in love through emails.

Rent or buy You’ve Got Mail on Amazon Video

Content Note: This one rates PG for some adult conversation.

15: Winter’s Tale

New York

Photo: Warner Bros. Pictures

This unique fantasy period drama tells the story of a man who sets out to save a woman he cannot quite remember, but feels a connection to. A dual timeline story, this one features Jessica Brown Findlay (Downton Abbey, Guernsey), and Colin Farrell as the star-crossed lovers.

Where to watch: rent or buy Winter’s Tale on Amazon Video.

Content Note: This film rates PG13 for some sexuality, and minor violence.

Bonus! Check out these other New York-centered Romantic-Comedies:

New York

Jennifer Lopez in Maid in Manhattan | Photo: Columbia Pictures

The Age of Innocence | Michelle Pfeiffer, Daniel Day-Lewis | PG | Watch on Amazon Prime (at time of publication)

Barefoot in the Park | Jane Fonda and Robert Redford | PG | Buy on Amazon Video

Breakfast at Tiffany’s | Audrey Hepburn | PG | Watch on Amazon Prime (at time of publication)

Carrie Pilby | Bel Powley, Colin O’Donoghue and William Moseley | PG13 | Rent or buy on Amazon Video or Stream on Netflix

Enchanted | Amy Adams and Patrick Dempsey | PG | Rent or Buy on Amazon Video

The Family Man | Nicholas Cage | PG13 | Rent or Buy on Amazon Video or stream on Netflix

Hitch | Will Smith | PG13 | Rent or Buy on Amazon Video

Maid in Manhattan | Jennifer Lopez | PG13 | Rent or Buy on Amazon Video

New York Minute | Ashley and Mary-Kate Olsen | PG | Rent or Buy on Amazon Video

New York, New York | Liza Minnelli and Robert De Niro | PG | Buy on Amazon DVD

Remember Me | Robert Pattinson, Emilie De Ravin | PG13 | Rent or Buy on Amazon Video

Sleepless in Seattle | Meg Ryan, Tom Hanks | PG | Amazon Prime

Two Weeks Notice | Sandra Bullock, Hugh Grant | PG13 | Rent or Buy on Amazon Video or watch on Netflix

When Harry Met Sally | Meg Ryan | R | Rent or Buy on Amazon Video


Tell me, have you seen any of these? Do you have a favorite from this list? Which romantic films would you add? Leave all of your comments and thoughts down in the comment section! I’d love to chat with you.

Featured image at top: Kate & Leopold. Photo – Miramax Films

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